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1.  2-sec-Butyl-1-(2-hy­droxy­eth­yl)-1H-benzimidazole-5-carboxylic acid 
In the title compound, C14H18N2O3, the carb­oxy­lic group is tilted by 12.00 (4)° with respect to the mean plane throught the benzimidazole ring system. The alcohol and carboxyl hydroxy groups are involved in intermolecular O—H⋯O and O—H⋯N hydrogen bonds, forming a two-dimensional network extending parallel the ab plane. The network is further stabilized by weak C—H⋯O inter­actions. The sec-butyl group is disordered over two sets of sites with refined occupancies of 0.484 (4) and 0.516 (4).
doi:10.1107/S1600536812023884
PMCID: PMC3393269  PMID: 22807826
2.  3β-Chloro-6-[2-(2-cyano­acet­yl)hydrazin-1-yl­idene]-5α-cholestane 
The asymmetric unit of the title compound, C30H48ClN3O, contains two mol­ecules, A and B. In both mol­ecules, the three cyclo­hexane rings in the steroid fused ring systems adopt chair conformations, while the cyclo­pentane rings adopt envelope and twist conformations in mol­ecules A and B, respectively. In mol­ecule B, the cyano group is disordered over two orientations with refined site-occupancies of 0.593 (8) and 0.407 (8). An intra­molecular C—H⋯N inter­action forms an S(10) ring in both mol­ecules. In the crystal, mol­ecules are linked by N—H⋯O, C—H⋯O and C—H⋯N inter­actions, resulting is chains propagating along the a-axis direction.
doi:10.1107/S1600536812009336
PMCID: PMC3344016  PMID: 22589925
3.  Ethyl 1-(2-hy­droxy­eth­yl)-2-(4-meth­oxy­phen­yl)-1H-benzimidazole-5-carboxyl­ate monohydrate 
In the title mol­ecule, C19H20N2O4·H2O, the benzimidazole ring system is essentially planar [maximum deviation = 0.013 (11) Å] and is inclined to the 4-meth­oxy­phenyl ring by 30.98 (5)°. In the crystal, O—H⋯O and O—H⋯N hydrogen bonds involving the water mol­ecule link neighbouring mol­ecules, forming a two-dimensional network lying parallel to the bc plane. There are also C—H⋯π and π–π inter­actions present. The latter involve inversion-related benzimidazole rings with centroid–centroid distances of 3.5552 (8) and 3.7466 (8) Å.
doi:10.1107/S1600536812001262
PMCID: PMC3275179  PMID: 22347035
4.  Ethyl 1-(2-hy­droxy­eth­yl)-2-[2-(methyl­sulfan­yl)eth­yl]-1H-benzimidazole-5-carboxyl­ate 
In the crystal structure of the title compound, C15H20N2O3S, the hy­droxy group is involved in the formation of O—H⋯N hydrogen bonds, which link two mol­ecules into a centrosymmetric dimer. Weak C—H⋯O hydrogen bonds further link these dimers into chains propagating along the a axis. The crystal packing exhibits π–π inter­actions between the five- and six-membered rings of neighbouring mol­ecules [centroid–centroid distance = 3.819 (2) Å] and short inter­molecular S⋯S contacts of 3.495 (1) Å.
doi:10.1107/S160053681105389X
PMCID: PMC3254533  PMID: 22259479
5.  2-Bromo-4-(3,4-dimethyl-5-phenyl-1,3-oxazolidin-2-yl)-6-meth­oxy­phenol 
In the title compound, C18H20BrNO3, the oxazolidine ring adopts an envelope conformation with the N atom at the flap position. The mean plane of oxazolidine ring makes dihedral angles of 82.96 (13) and 70.97 (12)°, respectively, with the phenyl and benzene rings. In the crystal, adjacent mol­ecules are connected via O—H⋯O and C—H⋯O hydrogen bonds and C—H⋯π inter­actions into a zigzag chain along the b axis.
doi:10.1107/S1600536811051269
PMCID: PMC3254397  PMID: 22259539
6.  Ethyl 2-(4-bromo­phen­yl)-1-sec-butyl-1H-benzimidazole-5-carboxyl­ate 
In the title compound, C20H21BrN2O2, the bromo­phenyl ring is twisted by 40.13 (8)° from the benzimidazole mean plane and the Br atom deviates by 0.753 (1) Å from that plane. The sec-butyl group is disordered over two conformations in a 0.898 (5):0.102 (5) ratio. In the crystal, mol­ecules related by translation along [10] are linked into chains via weak C—H⋯Br hydrogen bonds.
doi:10.1107/S1600536811048999
PMCID: PMC3239083  PMID: 22199931
7.  Ethyl 1-(butan-2-yl)-2-(2-meth­oxy­phen­yl)-1H-benzimidazole-5-carboxyl­ate 
In the title compound, C21H24N2O3, the mean planes of the benzene ring and the benzimidazole ring system form a dihedral angle of 69.94 (7)°. The ethyl group atoms of the ethano­ate fragment are disordered over two sets of sites, with refined occupancies of 0.742 (6) and 0.258 (6). In the crystal, there are weak C—H⋯N hydrogen bonds which connect mol­ecules into chains along the b axis. A weak inter­molecular C—H⋯π inter­action is also observed.
doi:10.1107/S1600536811046095
PMCID: PMC3238892  PMID: 22199745
8.  Ethyl 1-sec-butyl-2-(4-fluoro­phen­yl)-1H-benzimidazole-5-carboxyl­ate 
In the title compound, C20H21FN2O2, the benzene ring and the benzimidazole ring system are inclined at a dihedral angle of 44.40 (9)°. In the crystal, mol­ecules are linked by inter­molecular C—H⋯O hydrogen bonds, forming a zigzag chain along the b-axis direction. An intra­molecular C—H⋯π inter­action is also observed.
doi:10.1107/S1600536811041663
PMCID: PMC3247350  PMID: 22219968
9.  Ethyl 1-(2-hy­droxy­eth­yl)-2-propyl-1H-benzimidazole-5-carboxyl­ate 
In the title compound, C15H20N2O3, the benzimidazole ring is essentially planar, with a maximum deviation from the mean plane of 0.012 (1) Å. The crystal structure is stabilized by inter­molecular O—H⋯N hydrogen bonds, forming centrosymmetric dimers, which are connected in the [100] direction through weak C—H⋯O contacts.
doi:10.1107/S1600536811037421
PMCID: PMC3201285  PMID: 22058794
10.  11-[(E)-Benzyl­idene]-14-hy­droxy-8-phenyl-3,13-diaza­hepta­cyclo­[13.7.1.19,13.02,9.02,14.03,7.019,23]tetra­cosa-1(22),15,17,19(23),20-pentaen-10-one 
In the title compound, C35H30N2O2, the piperidine ring adopts a chair conformation and the pyrrolidine ring adopts an envelope conformation. The naphthalene ring makes dihedral angles of 24.56 (3) and 36.13 (4)° with the terminal phenyl rings. The dihedral angle between the two terminal phenyl rings is 55.27 (5)°. One of the C atoms in the pyrrolidine ring is disordered over two sites, with a refined occupany ratio of 0.670 (3):0.330 (3). An intra­molecular O—H⋯N hydrogen bond generates an S(6) ring. In the crystal structure, inversion dimers linked by pairs of C—H⋯O hydrogen bonds generate R 2 2(18) loops within sheets of mol­ecules lying parallel to the bc plane.
doi:10.1107/S1600536810043874
PMCID: PMC3011470  PMID: 21589358
11.  Ethyl 1-sec-butyl-2-(4-chloro­phen­yl)-1H-benzimidazole-5-carboxyl­ate 
In the title compound, C20H21ClN2O2, the ethyl 1H-benzimidazole-5-carboxyl­ate ring system, excluding the methyl­ene and methyl H atoms, is almost planar, with a maximum deviation of 0.055 (1) Å, and makes a dihedral angle of 40.63 (4)° with the benzene ring. The sec-butyl group is disordered over two positions, with refined site occupancies of 0.855 (4) and 0.145 (4). In the crystal, mol­ecules are linked into chains along [010] via inter­molecular C—H⋯O hydrogen bonds and are further inter­connected by C—H⋯Cl inter­actions into two-dimensional networks parallel to (001). The crystal structure is further consolidated by C—H⋯π inter­actions.
doi:10.1107/S1600536810033945
PMCID: PMC3008004  PMID: 21588740
12.  Ethyl 3-amino-4-[(2-hy­droxy­ethyl)­amino]benzoate 
In the crystal structure of the title compound, C11H16N2O3, mol­ecules are linked by one O—H⋯N and two N—H⋯O inter­molecular hydrogen bonds into a three-dimensional network, which incorporates R 2 2(14) and R 2 2(16) graph-set motifs.
doi:10.1107/S1600536810029077
PMCID: PMC3007246  PMID: 21588428
13.  2-Hy­droxy-16-[(E)-4-methyl­benzyl­idene]-13-(4-methyl­phen­yl)-12-phenyl-1,11-diaza­penta­cyclo­[12.3.1.02,10.03,8.010,14]octa­deca-3(8),4,6-triene-9,15-dione 
In the title compound, C37H32N2O3, an intra­molecular O—H⋯N hydrogen bond generates a five-membered ring, producing an S(5) motif. The piperidone ring adopts a half-chair conformation. The two fused pyrrolidine rings have similar envelope conformations. The interplanar angles between the benzene rings A/B and C/D are 75.68 (7) and 30.22 (6)°, respectively. In the crystal structure, adjacent mol­ecules are inter­connected into chains propagating along the [010] direction via inter­molecular C—H⋯O hydrogen bonds. Further stabilization is provided by weak C—H⋯π inter­actions.
doi:10.1107/S1600536810028357
PMCID: PMC3007522  PMID: 21588384
14.  Ethyl 1-(2-hy­droxy­eth­yl)-2-phenyl-1H-benzimidazole-5-carboxyl­ate 
There are two mol­ecules in the asymmetric unit of the title compound, C18H18N2O3. In each one, the benzimidazole ring system is essentially planar, with maximum deviations of 0.027 (1) and 0.032 (1)Å, and makes dihedral angles of 38.64 (6) and 41.48 (6)°, respectively, with the attached benzene rings. An intra­molecular C—H⋯O hydrogen bond is observed in each mol­ecule. The two independent mol­ecules are connected into a dimer by two inter­molecular O—H⋯N hydrogen bonds. In the crystal, mol­ecules form a two-dimensional layers parallel to (012) via weak inter­molecular C—H⋯O hydrogen bonds. In addition, weak π-π stacking inter­actions are observed with centroid–centroid distances of 3.5244 (12) and 3.6189 (12) Å.
doi:10.1107/S1600536810023639
PMCID: PMC3006730  PMID: 21588031
15.  Ethyl 1-(2-hy­droxy­eth­yl)-2-p-tolyl-1H-benzimidazole-5-carboxyl­ate 
The asymmetric unit of the title compound, C19H20N2O3, contains two mol­ecules (A and B) with slightly different orientations of the ethyl groups with respect to the attached carboxyl­ate groups. Intra­molecular C—H⋯O hydrogen bonds generate S(8) ring motifs in both mol­ecules A and B. In each mol­ecule, the benzimidazole ring system is essentially planar, with maximum deviations of 0.023 (1) and 0.020 (1) Å, respectively, for mol­ecules A and B. The dihedral angle between the benzimidazole ring system and the phenyl ring is 37.34 (5)° for mol­ecule A and 42.42 (5)° for mol­ecule B. In the crystal, O—H⋯N and C—H⋯O hydrogen bonds link the mol­ecules into [100] columns with a cross-section of two-mol­ecule by two-mol­ecule wide, and further stabilization is provided by weak C—H⋯π and π–π inter­actions [centroid separations = 3.5207 (7) and 3.6314 (8) Å].
doi:10.1107/S1600536810020799
PMCID: PMC3006903  PMID: 21587829
16.  9-(4-Hy­droxy-3-meth­oxy­phen­yl)-3,3,6,6-tetra­methyl-3,4,5,6-tetra­hydro-9H-xanthene-1,8(2H,7H)-dione 
In the title compound, C24H28O5, the two cyclo­hexene rings adopt envelope conformations, and the planes through the coplanar atoms makes dihedral angles of 82.86 (6) and 77.90 (6)° with the benzene ring. The two cyclo­hexene rings make a dihedral angle of 5.33 (6)° between their least-squares planes. The pyran ring adopts a flattened boat conformation. In the crystal packing, mol­ecules are linked into two-dimensional networks parallel to the ab plane via O—H⋯O and C—H⋯O inter­actions.
doi:10.1107/S1600536810020258
PMCID: PMC3007007  PMID: 21587786
17.  19-[(E)-4-Chloro­benzyl­idene]-16-(4-chloro­phen­yl)-2-hydr­oxy-1,11-diaza­hexa­cyclo­[15.3.1.02,10.03,8.010,17.011,15]henicosa-3(8),4,6-triene-9,18-dione 
In the title compound, C32H26Cl2N2O3, the piperidone ring adopts a chair conformation and the proline and pyrrolidine rings adopt envelope conformations. The indane ring system is essentially planar with an r.m.s. deviation of 0.011 Å for the non-H atoms. The dihedral angle between the two chloro-substituted benzene rings is 63.69 (10)°. Intra­molecular C—H⋯O and N—H⋯O hydrogen bonds may influence the mol­ecular conformation. In the crystal structure, mol­ecules are connected into layers by weak inter­molecular C—H⋯O hydrogen bonds.
doi:10.1107/S1600536810018611
PMCID: PMC2979351  PMID: 21579517
18.  Ethyl 1-sec-butyl-2-(2-hydroxy­phen­yl)-1H-benzimidazole-5-carboxyl­ate 0.25-hydrate 
In the title compound, C20H22N2O3·0.25H2O, the water mol­ecule (occupancy 0.25) is disordered across a crystallographic inversion center. The dihedral angle between the hydroxy­phenyl ring and the benzimidazole ring system is 59.31 (9)°. In the crystal structure, mol­ecules are connected by inter­molecular O—H⋯N and C—H⋯O hydrogen bonds. The crystal structure is further stabilized by a weak C—H⋯π inter­action involving the imidazole ring.
doi:10.1107/S1600536810015448
PMCID: PMC2979540  PMID: 21579384
19.  Ethyl 1-sec-butyl-2-p-tolyl-1H-benzimidazole-5-carboxyl­ate 
In the title compound, C21H24N2O2, the butyl group is disordered over two orientations with refined site occupancies of 0.883 (3) and 0.117 (3). The dihedral angle between the mean plane of benzimidazole ring system and the benzene ring is 39.32 (4)° and the dihedral angle between the mean plane of carboxyl­ate group and the benzimidazole ring system is 6.87 (5)°. A weak intra­molecular C—H⋯π inter­action may have some influence on the conformation of the mol­ecule. In the crystal structure, mol­ecules are linked into infinite chains along the b axis by weak inter­molecular C—H⋯O hydrogen bonds.
doi:10.1107/S1600536810015242
PMCID: PMC2979236  PMID: 21579242
20.  Ethyl 1-tert-butyl-2-(4-hydr­oxy-3-methoxy­phen­yl)-1H-benzimidazole-5-carboxyl­ate 
In the title compound, C21H24N2O4, the benzimidazole ring system is almost planar, with a maximum deviation of 0.047 (1) Å and makes a dihedral angle of 88.44 (5)° with the attached benzene ring. In the crystal, mol­ecules form infinite chains along the b axis by way of inter­molecular O—H⋯N and C—H⋯O inter­actions. Weak C—H⋯π also contribute to the stabilization of the crystal structure.
doi:10.1107/S1600536810011918
PMCID: PMC2979157  PMID: 21579111
21.  Ethyl 1-sec-butyl-2-(4-methoxy­phen­yl)-1H-benzimidazole-5-carboxyl­ate 
In the title mol­ecule, C21H24N2O3, the dihedral angle between the benzene and imidazole rings is 66.33 (13)°. The imidazole ring is essentially planar, with a maximum deviation of 0.004 (2) Å. In the crystal structure, mol­ecules are connected by weak C—H⋯O hydrogen bonds, forming chains along the b axis
doi:10.1107/S1600536810007634
PMCID: PMC2983837  PMID: 21580670
22.  Ethyl 4-(2-hydroxy­ethyl­amino)-3-nitro­benzoate 
In the title compound, C11H14N2O5, the mol­ecular structure is stabilized by an intra­molecular N—H⋯O hydrogen bond, which generates an S(6) ring motif. The nitro group is twisted slightly from the attached benzene ring, forming a dihedral angle of 5.2 (2)°. In the crystal packing, inter­molecular O—H⋯O and C—H⋯O hydrogen bonds link the mol­ecules into a three-dimensional network. The crystal studied was a non-merohedral twin, the refined ratio of the twin components being 0.264 (2):0.736 (2).
doi:10.1107/S1600536810008147
PMCID: PMC2983846  PMID: 21580671
23.  Ethyl 1-sec-butyl-2-phenyl-1H-benzimidazole-5-carboxyl­ate 
In the title mol­ecule, C20H22N2O2, the benzimidazole ring system is essentially planar, with a maximum deviation of 0.024 (1) Å. The dihedral angle between the phenyl and benzimidazole ring system is 43.71 (5)°. The atoms of the butyl group are disordered over two sets of sites with occupancies of 0.900 (4) and 0.100 (4). In the crystal structure, mol­ecules are connected by weak inter­molecular C—H⋯O hydrogen bonds, forming chains along the b axis. The crystal structure is further stabilized by C—H⋯π inter­actions.
doi:10.1107/S160053681000872X
PMCID: PMC2984087  PMID: 21580635
24.  Ethyl 1-tert-butyl-2-(4-methoxy­phen­yl)-1H-benzimidazole-5-carboxyl­ate 
In the title mol­ecule, C21H24N2O3, the imidazole ring is essentially planar, with a maxium deviation of 0.015 (1) Å. The dihedral angle between the benzene and imidazole rings is 65.47 (6)°. The crystal packing is stabilized by weak inter­molecular C—H⋯O and C—H⋯N hydrogen bonds, forming zigzag chains along the c axis. The crystal structure is further stabilized by C—H⋯π inter­actions.
doi:10.1107/S1600536810007956
PMCID: PMC2984033  PMID: 21580619
25.  Dimethyl­ammonium 5,5-dimethyl-3-oxo-2-(3,3,6,6-tetra­methyl-1,8-dioxo-2,3,4,5,6,7,8,9-octa­hydro-1H-xanthen-9-yl)cyclo­hex-1-enolate 9-(2-hydr­oxy-4,4-dimethyl-6-oxocyclo­hex-1-en­yl)-3,3,6,6-tetra­methyl-3,4,5,6,7,9-hexa­hydro-1H-xanthene-1,8(2H)-dione n-hexane hemisolvate monohydrate 
The main mol­ecule of the title compound, C2H8N+·C25H31O5 −·C25H32O5·0.5C6H14·H2O, exists as two crystallographically independent mol­ecules, the hydr­oxy group of one being deprotonated. The pyran rings of both independent units adopt boat conformations. One of the two cyclo­hexene rings of the xanthene unit adopts an envelope conformation whereas the other is in a half-chair conformation. The cyclo­hexene ring attached to the xanthene unit adopts an envelope conformation. The n-hexane solvent mol­ecule is disordered about a crystallographic glide plane and the symmetry-independent components are again disordered over two positions, each with an occupancy of 0.25. In the crystal structure, the xanthene derivatives are linked by O—H⋯O, N—H⋯O and C—H⋯O hydrogen bonds, forming a three-dimensional network with channels along the a axis. The dimethyl­ammonium cations and water mol­ecules lie in small channels and are linked to the framework via O—H.·O and N—H⋯O hydrogen bonds. The n-hexane solvent mol­ecules occupy large channels.
doi:10.1107/S1600536810003107
PMCID: PMC2979890  PMID: 21579881

Results 1-25 (35)